Diethyl Ether → HCID 22632112, compound

HRID 1586972Notes

Reaction equation

HRID 1586972 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19].CCOCC>O1CCCC1.CN(C)C=O.O>[Br:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:20]([CH2:21][CH3:22])[CH2:18][CH3:19])=[O:9])=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 8021DiethylamineHCID 225994-(Bromomethyl)benzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 22632112HCID 22632112, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Bromomethylbenzoic acid (50 g, 233 mmol) is dissolved in 500 mL of tetrahydrofuran containing a few drops if N,N-dimethylformamide at room temperature under nitrogen and treated dropwise over 1 hour with oxalyl chloride (268 mmol, 34.0 g, 23.4 mL). After the addition, the reaction mixture is stirred for 0.5 hour, at which point the solvent is removed in vacuo. The solid residue is dissolved in 200 mL of tetrahydrofuran and poured into a rapidly stirring solution of diethylamine (536 mmol, 39.2 g, 55.7 mL) in 400 mL of water. After the mixture cools to room temperature, 100 mL of ether are added and the two phases are separated. The organic phase is dried over magnesium sulfate and concentrated in vacuo affording 54.01 g (200 mmol, 86% yield) of the product as a white solid.

Workup

  1. additionAfter the addition
  2. customis removed in vacuo
  3. dissolutionThe solid residue is dissolved in 200 mL of tetrahydrofuran
  4. customcools to room temperature
  5. customthe two phases are separated
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62ff2bcae26e4675a7d72b4e0a18d7c2
Source dataset
uspto-grants-1993_06
Patent number
US05216165

Reaction notes

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